Brønsted acid catalysed eco friendly synthesis of quaternary centred C-3 functionalized oxindole derivatives

Poomathi, Nataraj ; Balaji, Ravichandran ; Maheswari, Narayanan Uma ; Mathivanan, Narayanasamy ; Perumal, Paramasivan T. ; Balasubramanian, Kalpattu K. ; Barathi, Veluchamy Amutha ; Ramakrishna, Seeram (2018) Brønsted acid catalysed eco friendly synthesis of quaternary centred C-3 functionalized oxindole derivatives New Journal of Chemistry, 42 (18). pp. 14817-14826. ISSN 1144-0546

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Official URL: http://doi.org/10.1039/C8NJ02276C

Related URL: http://dx.doi.org/10.1039/C8NJ02276C

Abstract

A facile atom economic and eco friendly protocol for the synthesis of biologically important quaternary centered C-3 functionalized oxindole derivatives, with a novel nucleus, in high yields has been demonstrated by employing 3-hydroxy-2-oxindole, isoxazolone/pyrazolone and environmentally benevolent p-toluene sulphonic acid as a catalyst. The advantages of this protocol are the wide substrate scope, practical simplicity, benign solvent and good yields. All the synthesized compounds were evaluated for their in vitro anti-microbial activity. Several compounds exhibited good activities comparable to those of established standard drugs. Furthermore, the anti-cancer activity of compounds 3g and 3m has been preliminarly demonstrated by in vitro evaluation against human tumor cell lines MCF-7 and Hep-2, using MTT-based assays with commercially available standard drug cisplatin as a positive control. Gratifyingly, compounds 3g and 3m exhibited good in vitro inhibitory activities against Hep-2 and MCF-7 cell lines. These results indicate that 3-indolyl oxindole substituted isoxazole analogs may be potential lead compounds for further biological screening.

Item Type:Article
Source:Copyright of this article belongs to Royal Society of Chemistry.
ID Code:128933
Deposited On:07 Nov 2022 05:01
Last Modified:31 Jan 2023 08:27

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